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Sex With Steph: Help! I’m A 25-Year-Old Virgin

I stumbled upon your column today from an outside website, and if possible, I’d love to get some advice on a subject that has been plaguing me for too many years. I’m 25 years old, and … I’m still a virgin.


I have had plenty of dates and several longer-term boyfriends in the last 10 years, and I normally have no trouble climaxing from other methods, like “outercourse” and oral sex. I’m comfortable being naked around the guys I’ve been in relationships with, so I don’t think that’s the issue. Through high school, college, and the year after, I dated some great guys, but the majority of them were also virgins or pretty inexperienced, and either for religious or other reasons they didn’t push the issue too much, so I always sort of assumed it would happen when I was ready and the time was right.

Problem is, a few years ago I decided I was … mentally ready, I guess … I went to the gyno and got on birth control, but even now in a serious relationship again, I cannot bring myself to have intercourse, because faced with the sudden realization of doing it I am SCARED out of my mind. I don’t even know who to talk to about it. I guess I fear the penetration … that it will hurt like heck, that I will hate it and never want to do it again and so on. I somehow just don’t believe it will fit! I honestly have never even used a tampon, so I have no idea what it might feel like. Even going to the Dr. and having him do a pap smear was an extremely frightening experience! Yes, you can laugh at that for a minute, I even laugh at how ridiculous I am sometimes.

Though I have managed to be very successful and sane in other aspects of my life. But I am so stressed out, constantly torn between “just wanting to get it over with already,” since I’m sure it’s not the horrific event I imagine it to be if everyone else on the planet does it, and being too afraid when the time comes. I don’t want to meet the man of my dreams one day (if the guy I’m dating now isn’t my future husband) and still be too afraid to sleep with him.

Please, please help. Are there any tips or advice you can give me on how to make first-time sex easier, or what might make it more manageable? Tranquilizers maybe?! But in all seriousness, I’m losing my mind here — and all I want to lose is my freakin virginity already!!

Hey there, girlfriend!

First of all, can we be BFFs? I love the sense of humor you have with what can be an awkwardly intimate subject, and I also love how self-aware you are about everything you’re feeling. Considering how long you’ve waited to have sex (um … not that 25 makes you a decrepit, old spinster but, at the age of 19, I felt that I was the last amongst my friends to have sex), the emotions you’re feeling make complete sense. I’d also like to take a moment to commend you on your creativity in the bedroom. It only highlights the fact that intercourse itself doesn’t have to be the main attraction, and that there is pleasure to be had in a variety of other ways. Hello, dry humping, fingering, etc.

You seem spot-on with your own self-assessment. You’ve built up that final sexual step in your mind so much that it now seems almost insurmountable. So let’s tackle those two main fears head-on: the fear of pain, and the fear of Bad Sex. As far as the pain goes, I swear I wasn’t giggling when you mentioned that pap smears were horrifying. Or if I was, it was only because I find them equally horrifying. They’re for the most part uncomfortable, awkward, and invasive, and I still don’t understand why the paper robes they provide for you before your examination are the size of a flipping napkin. What’s not to hate? But sex doesn’t have to be that way.

People experience varying levels of pain and/or discomfort the first time they have sex, especially if their hymen wasn’t previously broken via tampon usage, fingering, or an aggressive experience with a mechanical bull. Some first-timers experience heavy bleeding. For others, that penis slides in smooth as silk, though how pleasant the experience as a whole will be is still far from guaranteed. Any time you have sex with someone for the first time can be awkward, simply because … it’s the first time, and you need to give yourselves a chance to get in sync, and learn the best ways to turn each other on.

As far as the pain goes, you can take measures to diminish its probability:

1. Foreplay. The more he plays around down there with his tongue and his finger(s), the better prepared your vagina will be for his penis. After he’s rubbed your clitoris into submission — and perhaps even produced an orgasm or two — have him ease a finger in, and then another one, for the purposes of doing some gentle exploring. If he turns his hand palm up and flicks his fingers in a come-hither gesture, he may even find your g-spot!

2. Even more foreplay. All that rubbing and stroking and poking shouldn’t merely be used as a means to prepare your vagina for penetration. Its intention should also be to get you aroused. Because, if you’re not aroused, it ain’t gonna be pleasant.

3. Lube! Lube may actually be in my top five list of most favorite things ever. Or at least the top 10. Because books, cats, hula hoops, and candy buttons are totally up there as well. When it comes to sex play, lube is tops because while some natural lubrication as a result of arousal is key, some additional lubrication can certainly help. So when you’re ready for that final step, apply some lube, and then tell yourself to relax — and have fun, dammit!

As for the fear that you “will hate it and never want to do it again,” you can’t expect that your first time will necessarily be mind-blowing. Such expectations will only place added pressure on the entire experience and, as I mentioned above, first time sex can often be awkward. Those smooth-as-heck sex scenes they show in theaters? Ha! Please. Just know that the more you get to know your partner’s body and specific turn-ons, and the more he gets to know yours, the better sex will become.

Got a question for “Sex with Steph” sex adviser Steph Auteri? Send her an email with your pressing sex questions!

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